Biomaterial Database

Synthesis of 2-acetamido-2-deoxy-3-O-beta-D-mannopyranosyl-D-glucose. 1976

M A Shaban, and R W Jeanloz

Condensation of 4,6-di-O-acetyl-2,3-O-carbonyl-alpha-D-mannopyranosyl bromide with benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-alpha-D-glucopyranoside (2) gave an alpha-D-linked disaccharide, further transformed by removal of the carbonyl and benzylidene groups and acetylation into the previously reported benzyl 2-acetamido-4,6-O-benzylidene groups and acetylation into the previously reported benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl)-alpha-D-glucopyranoside. Condensation of 3,4,6-tri-O-benzyl-1,2,-O-(l-ethoxyethylidene)-alpha-D-glucopyranose or 2-O-acetyl-3,4,6-tri-O-benzyl-alpha-D-glucopyranosyl bromide with 2 gave benzyl 2-acetamido-3-O-(2 O-acetyl-3,4,6-tri-O-benzyl-beta-D-glucopyranosyl)-4,6-O-benzylidene-2-deoxy-alpha-D-glucopyranoside. Removal of the acetyl group at O-2, followed by oxidation with acetic anhydride-dimethyl sulfoxide, gave the beta-D-arabino-hexosid-2-ulose 14. Reduction with sodium borohydride, and removal of the protective groups, gave 2-acetamido-2-deoxy-3-O-beta-D-mannopyranosyl-D-glucose, which was characterized as the heptaacetate. The anomeric configuration of the glycosidic linkage was ascertained by comparison with the alpha-D-linked analog.

UI	MeSH Term	Description	Entries
D008358	Mannose	A hexose or fermentable monosaccharide and isomer of glucose from manna, the ash Fraxinus ornus and related plants. (From Grant & Hackh's Chemical Dictionary, 5th ed & Random House Unabridged Dictionary, 2d ed)	D-Mannose,Mannopyranose,Mannopyranoside,D Mannose
D008722	Methods	A series of steps taken in order to conduct research.	Techniques,Methodological Studies,Methodological Study,Procedures,Studies, Methodological,Study, Methodological,Method,Procedure,Technique
D009904	Optical Rotation	The rotation of linearly polarized light as it passes through various media.	Optical Activity,Activity, Optical,Rotation, Optical
D004187	Disaccharides	Oligosaccharides containing two monosaccharide units linked by a glycosidic bond.	Disaccharide
D005947	Glucose	A primary source of energy for living organisms. It is naturally occurring and is found in fruits and other parts of plants in its free state. It is used therapeutically in fluid and nutrient replacement.	Dextrose,Anhydrous Dextrose,D-Glucose,Glucose Monohydrate,Glucose, (DL)-Isomer,Glucose, (alpha-D)-Isomer,Glucose, (beta-D)-Isomer,D Glucose,Dextrose, Anhydrous,Monohydrate, Glucose
D005960	Glucosides	A GLYCOSIDE that is derived from GLUCOSE.	Glucoside
D006027	Glycosides	Any compound that contains a constituent sugar, in which the hydroxyl group attached to the first carbon is substituted by an alcoholic, phenolic, or other group. They are named specifically for the sugar contained, such as glucoside (glucose), pentoside (pentose), fructoside (fructose), etc. Upon hydrolysis, a sugar and nonsugar component (aglycone) are formed. (From Dorland, 28th ed; From Miall's Dictionary of Chemistry, 5th ed)	Glycoside
D006595	Hexosamines	AMINO SUGARS created by adding an amine group to a hexose sugar.	Hexosamine
D013055	Spectrophotometry, Infrared	Spectrophotometry in the infrared region, usually for the purpose of chemical analysis through measurement of absorption spectra associated with rotational and vibrational energy levels of molecules. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	IR Spectra,Infrared Spectrophotometry,IR Spectras,Spectra, IR